Table of contents

1. A Review of General Chemistry5h 5m
2. Molecular Representations1h 14m
3. Acids and Bases2h 46m
4. Alkanes and Cycloalkanes4h 17m
5. Chirality3h 39m
6. Thermodynamics and Kinetics1h 22m
7. Substitution Reactions1h 48m
8. Elimination Reactions2h 30m
9. Alkenes and Alkynes2h 9m
10. Addition Reactions3h 19m
11. Radical Reactions1h 58m
12. Alcohols, Ethers, Epoxides and Thiols2h 42m
13. Alcohols and Carbonyl Compounds2h 17m
14. Synthetic Techniques1h 26m
15. Analytical Techniques:IR, NMR, Mass Spect7h 3m
16. Conjugated Systems6h 13m
17. Ultraviolet Spectroscopy51m
18. Aromaticity2h 34m
19. Reactions of Aromatics: EAS and Beyond5h 1m
20. Phenols55m
21. Aldehydes and Ketones: Nucleophilic Addition4h 56m
22. Carboxylic Acid Derivatives: NAS2h 51m
23. The Chemistry of Thioesters, Phophate Ester and Phosphate Anhydrides1h 10m
24. Enolate Chemistry: Reactions at the Alpha-Carbon1h 53m
25. Condensation Chemistry2h 9m
26. Amines1h 43m
27. Heterocycles2h 0m
28. Carbohydrates5h 53m
29. Amino Acids4h 20m
30. Peptides and Proteins2h 42m
31. Catalysis in Organic Reactions1h 30m
32. Lipids 2h 50m
33. The Organic Chemistry of Metabolic Pathways2h 52m
34. Nucleic Acids1h 32m
35. Transition Metals6h 14m
36. Synthetic Polymers1h 49m

10. Addition Reactions

Ozonolysis

Organic Chemistry

10. Addition Reactions

Ozonolysis

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Problem 45e(vii,viii)

Textbook Question

Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (vii) 1. mCPBA 2. (viii) 1. O₃ 2. CH₃SCH₃.
(e)

Verified step by step guidance

Step 1: Analyze the given alkene structure. The molecule contains a double bond, which is the reactive site for the reactions described.

Step 2: For reaction (vii) with mCPBA, understand that mCPBA (meta-chloroperoxybenzoic acid) is a reagent used for epoxidation. It reacts with the double bond to form an epoxide. The oxygen from mCPBA is added across the double bond, creating a three-membered cyclic ether (epoxide).

Step 3: For reaction (viii) with O₃ followed by CH₃SCH₃, recognize that this is an ozonolysis reaction. Ozone (O₃) cleaves the double bond, breaking it into two fragments. The second step with CH₃SCH₃ (dimethyl sulfide) is a reductive workup, which converts the ozonolysis products into aldehydes or ketones depending on the substitution pattern of the double bond.

Step 4: Determine the products for each reaction based on the structure of the alkene. For the epoxidation (vii), the double bond will form an epoxide. For the ozonolysis (viii), the double bond will be cleaved, and the resulting fragments will be aldehydes or ketones.

Step 5: Draw the products for each reaction. For (vii), draw the epoxide structure where the oxygen is added across the double bond. For (viii), draw the aldehyde or ketone fragments resulting from the cleavage of the double bond. Ensure the correct connectivity and substitution patterns are maintained in the products.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Epoxidation

Epoxidation is a reaction where an alkene is converted into an epoxide, a three-membered cyclic ether. This transformation typically occurs using peracids, such as m-chloroperbenzoic acid (mCPBA). The reaction involves the electrophilic attack of the peracid on the double bond, resulting in the formation of the epoxide and a carboxylic acid byproduct.

Ozonolysis

Ozonolysis is a reaction involving the cleavage of alkenes using ozone (O₃) to form carbonyl compounds, such as aldehydes and ketones. The reaction proceeds through the formation of a molozonide intermediate, which rearranges to yield ozonides that can be further reduced. In this case, the presence of dimethyl sulfide (CH₃SCH₃) serves as a reducing agent to convert the ozonides into stable carbonyl products.

Stereochemistry of Reactions

Stereochemistry refers to the spatial arrangement of atoms in molecules and how this affects their chemical behavior. In reactions involving alkenes, the stereochemistry can influence the products formed, especially in reactions like epoxidation and ozonolysis. Understanding the stereochemical outcomes is crucial for predicting the specific products, as different configurations can lead to different isomers.

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Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (vii) 1. mCPBA 2. (viii) 1. O3 2. CH3SCH3.(e)

Key Concepts

Epoxidation

Ozonolysis

Stereochemistry of Reactions

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Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (vii) 1. mCPBA 2. (viii) 1. O₃ 2. CH₃SCH₃.
(e)